What if most individual stocks actually don't outperform and a small handful of massive winners are doing all the heavy lifting? In this episode, renowned finance professor Hank Bessembinder joins the show to break down decades of research on market returns, stock picking, and why diversification matters far more than most investors realize. We unpack his groundbreaking findings on market skewness and explain why identifying winning stocks is far harder than social media and headlines suggest.

Take The Pilot Wealth Index to find out if you are on track for retirement!

You can find show notes, resources and more at: https://tinyurl.com/3kef3pdx

What if we're asking the wrong question about market peaks, bubbles, and crashes? Everyone wants to know what happens next, but this episode shifts the focus to what you can actually control: risk, timing, and smart decision-making. Today's conversation breaks down the most common fears investors face — from AI bubbles to gold hype to stock market pullbacks — and gives you a grounded lens for evaluating what's real versus what's noise.

Take The Pilot Wealth Index to find out if you are on track for retirement!

You can find show notes, resources and more at: https://tinyurl.com/2d3z463u

What happens when success, identity, and purpose collide with some of the hardest battles a person can face? In this powerful conversation with Ryan Watson, we explore the realities many pilots and high-performing professionals quietly carry: addiction, mental health struggles and the pressure to appear "perfect" in an industry where vulnerability can feel dangerous. Ryan opens up about the challenges he faced, the misconceptions around struggle, and the hidden cultural stigma that keeps so many silent.

Take The Pilot Wealth Index to find out if you are on track for retirement!

You can find show notes, resources and more at: https://tinyurl.com/4ahwrx8w

Are private equity and alternative investments really the secret weapon of the wealthy or are public markets still your best bet? In this episode, we tackle one of the most common questions we hear: should you look beyond the stock market? We'll break down what private equity really is, who it's for, and why some companies stay private instead of going public. You'll learn how these investments work, why they're not always the golden ticket they appear to be, and how to think critically about diversifying your portfolio.

Take The Pilot Wealth Index to find out if you are on track for retirement!

You can find show notes, resources and more at: https://tinyurl.com/2eyuv9n8

Why do airlines struggle to make money even when planes are full? In this episode, we unpack the surprising economics behind one of the world's most essential yet fragile industries. From razor-thin profit margins to the ripple effects of global shocks like COVID-19, you'll learn why airlines operate on such precarious financial ground and what it takes for them to stay in the air.

Take The Pilot Wealth Index to find out if you are on track for retirement!

You can find show notes, resources and more at: https://tinyurl.com/ypwpywzf

What do the new Secure Act 2.0 rules mean for Roth contributions and retirement planning in 2025? In this episode, we explore what pilots and high-income earners need to know about Roth catch-up contributions, required Roth designations, and the risks of in-plan Roth conversions. You'll also learn how these changes may impact your taxes, your long-term retirement savings, and the best ways to prepare now.

Take The Pilot Wealth Index to find out if you are on track for retirement!

You can find show notes, resources and more at: https://tinyurl.com/2f6srj8e

What actually makes for a happy, fulfilling retirement? Is it all about the numbers, or is there more to the story? In this episode, Dr. Michael Finke—professor, researcher, and one of the most respected voices in retirement planning—shares his groundbreaking research on what truly drives satisfaction in retirement. Drawing from decades of data, interviews, and insights from retirees themselves, Dr. Finke uncovers the three essential pillars of a rewarding life after work.

Take The Pilot Wealth Index to find out if you are on track for retirement!

You can find show notes, resources and more at: https://tinyurl.com/bwvxsd69

What exactly is private equity, and why is it suddenly being linked to your 401(k)? In this episode, we break down the recent executive order that directs the Department of Labor to explore ways of including private equity in retirement plans. You'll learn what sets private equity apart from the public markets you're familiar with, why it excites some investors, and why others aren't as enthusiastic.

Take The Pilot Wealth Index to find out if you are on track for retirement!

You can find show notes, resources and more at: https://tinyurl.com/39xt6s9c

How can you avoid running out of money in retirement and still live the life you want? In this episode, we break down the most important strategies for sustainable retirement spending. You'll learn how retirement spending actually works in real life and why your financial plan needs to adjust as your lifestyle and health change over time. Whether you're a do-it-yourself planner or prefer to delegate, you'll walk away with practical steps for knowing your expenses, stress-testing your plan, and creating a retirement strategy that helps you spend confidently without fear of running out.

Take The Pilot Wealth Index to find out if you are on track for retirement!

You can find show notes, resources and more at: https://tinyurl.com/c2r2hsp9

Is Social Security really running out of money, or is that just a headline meant to scare you? In this episode, we cut through the noise to uncover the truth about its future, its viability, and how it actually works. You'll learn how to separate political fear tactics from the facts, why the "trust fund bankruptcy" story isn't the whole picture, and how your claiming strategy could mean hundreds of thousands of dollars gained or lost over your lifetime.

Take The Pilot Wealth Index to find out if you are on track for retirement!

You can find show notes, resources and more at: https://tinyurl.com/4cr6bm56